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Org Lett. 2012 Aug 3;14(15):3912-5. doi: 10.1021/ol301660f. Epub 2012 Jul 24.

Gold-catalyzed hydrosilyloxylation driving tandem aldol and Mannich reactions.

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  • 1Department of Chemistry, Kangwon National University, Chuncheon 200-701, Republic of Korea.


The chemoselective formation of an enolate from alkyne in the presence of a carbonyl and imine group was realized, which constructed a variety of structural motifs under exceedingly mild reaction conditions in a tandem process. Reaction driving tandem hydrosilyloxylation/aldol reactions was achieved through the formation of enol silyl ethers catalytically generated in situ from readily available alkynes. These reactions were expanded to obtain β-amino enol silyl ethers in good yields via the tandem hydrosilyloxylation/isomerization/Mannich reaction.

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